Always a First Time
by Mindy35
Summary: Jack/Liz. The events of season one through Jack's eyes.
1. Chapter 1

Title: Always a First Time

Author: Mindy

Rating: K.

Disclaimer: I'm not ready for the big chair. It and they belong to Tina et al.

Spoilers: Pilot, "Blind Date", "Jack Meets Dennis", "Black Tie", "Corporate Crush", "Hiatus" and more…

Summary: Jack/Liz. The events of season one through Jack's eyes.

A/N: I began this story ages ago. It goes into far too much detail on Liz and Jack's relationship, but if that's your thing, as it is mine-- please read on. I planned to continue this into season 2 and have written part of it. But I was struggling a little, so I thought I'd post this first. Any feedback would be much appreciated.

I.

_Spark_

Jack could remember that first meeting with Liz Lemon like it was yesterday.

He remembered the first time he shook her hand, quite perfunctorily. He remembered giving her a quick once-over, taking in the dark jeans and budget blazer that he would later come to recognise as Lemon's uniform. He recalled the first time she glowered at him in that distinctly undisguised style and pinned him with her unrepentantly sour tone. And he remembered warmly the first of what would become various memorably clumsy exits she made from his office.

But it struck him now as strange that there was no perceptible warning, no indication, however slight, of what was to come. Usually, before a thunderstorm, there's the spark of lightning. Before a tornado, there is a gust of wind. And, usually, before he faced any new opponent or challenge, Jack felt some intrinsic sense of foreboding or excitement.

The hairs on his neck might stand up on end or there would be an anticipatory rumbling in his gut. He liked that feeling – it gave him an edge, a rush. But there was absolutely no warning when Liz Lemon walked into his immaculately ordered and comfortable life. And he really felt there should have been one.

For the first time in Jack's life, his considerable and fundamental instincts had failed him.

_Scheme_

The first time Jack wondered whether Liz Lemon might be gay was when he mentioned her on the phone to his old pal from Plastics. Privately, he couldn't help but note the remarkable similarities between the two women.

When he first met Gretchen Thomas, she was not the Amazonian Goddess she had since morphed into. She'd had a short mannish haircut, hid a pretty face behind outdated frames and had no clue what to do with her long limbs. Before he took her under his wing, he never saw her in a dress above once a year and knew for a fact that she spent most of her evenings staring at her computer screen.

She also didn't like him very much, which was not only hard for him to understand, but most unusual for any member of the opposite sex. Something was undeniably amiss. Then, one day, partway through her transformation from ugly ducking to gorgeous swan, he caught Thomas flirting with the girl who delivered coffee to their offices. And suddenly, Jack understood completely.

He couldn't help feeling it was a bit of a shame though. After Gretchen had begrudgingly accepted his mentorship, he'd started to quite enjoy her company, and felt her opinion gradually shifting as well. The closer and more comfortable they became with each other, he'd often found himself lamenting that, if not for her sexual inclination, Gretchen might've been his perfect woman. Only excepting that on the whole, he tended to be far more attracted to brunettes.

But Gretchen had other qualities that he slowly grew to appreciate. He'd never been a fan of stupid women – not in the long term anyhow -- and Gretchen had one of the sharpest minds he'd ever come across. It was also rare to find someone in their field with a decent sense-of-humour, but as she came out of her homely shell, so did her more cheeky, mellow side. She was also not unpleasant to look at, easy to be around and the one person in his daily life who would always tell him the absolute, unadulterated truth.

When he met Liz Lemon, she also didn't like him very much. An opinion which, gay or no, he was sure he could reverse. She also needed his help more than she'd ever admit, and he liked her company more than _he'd_ ever admit. There was a swan to be uncovered and he was just the man to do it.

But, for whatever reason, he was utterly loath to wait around and see if he caught Lemon flirting with any coffee girls. Or found out through office gossip that one of the bra-less female writers at her table was her clandestine lover. He was not entirely convinced it was her preference, but this time, it seemed imperative that he know for certain.

Which was why he'd set Liz up with Gretchen. At the most, he'd have made two lonely gays very, very happy and he'd be toasted at their civil ceremony. And at the very least, they would have something in common to talk about. Him -- which didn't bother him one bit. By then, Gretchen was one of his biggest advocates and only true friends. Perhaps she could influence Liz into seeing him in a more generous light.

Another advantage of setting up the match was that without doubt, he would hear about the outcome of their date through one or both of them. And he certainly didn't have to wait long. Gretchen had phoned him as soon as she'd gotten home, accusing him of setting her up with someone _he_ himself was interested in for the express purpose of gleaning information about her sexual proclivity.

According to her, _Liz _was his perfect woman. That was the downside of having close friends. They knew you, and your tactics, far too well to be oblivious to being manipulated.

Still, the wine she'd drunk at dinner had mellowed Gretchen's outrage somewhat and, as he reasoned, an evening out with an entertaining dinner companion, whether the companion turned out to be her future bride or not, could not do her any harm. Gretchen was mostly placated by the fact that she had truly enjoyed meeting Liz, which inexplicably pleased Jack a great deal.

What pleased him more -- but which he did not admit to his friend -- was that his little scheme had succeeded exactly the way he'd hoped it would. Even before she slopped into his office the next day, with that peevish look and tone he was starting to rather relish, Jack knew that Lemon was one hundred percent straight. And he couldn't resist a smug, secret smile.

He now had substantial reason to believe that, despite any protestations she might make to the contrary if he were actually to verbalise such a suspicion, Liz Lemon was as sexually susceptible as the next woman. That beneath the obvious misrepresentation of her drab garb and prickly reserve, her heart beat the rhythm of a passionate, heterosexual woman.

It was only later that something struck him as odd about that. Because it meant that Lemon genuinely disliked him for reasons not related to enraged lesbianism. It was not men in general that repelled her. But him -- certified, non-genius Jack Donaghy.

Why it bothered him so, apart from it being such an uncommon occurrence, was unclear. But it was more unsettling to him than it should be. After all, he had it all – charm, wealth, influence, looks, smarts, sex appeal and more. But apparently, none of it was working on Liz Lemon.

Clearly, there was a first time for everything.

_TBC…_


	2. Chapter 2

Title: Always a first Time

Author: Mindy

-x-

_Pang_

He remembered the first time she called him 'friend', the first time he realised that Liz actually viewed him as one. He doubted she noticed that she'd let the accidental admission slip.

It was during one of her rants about Dennis, one of those rows where Lemon didn't necessarily need him to contribute a word. He just stood at the back of the elevator and let her have at him, her eyes flashing and mouth running away with her. He had to admit, it was a side of her he found quite…..exhilarating.

Mid-rant, she'd half-turned and informed him haughtily over her shoulder that she had plenty of friends she could talk to. And a little bell had gone off in Jack's mind. Liz counted _him_ as one of her friends. He didn't know why he was so surprised at the time. He'd set out to become her friend and what Jack Donaghy put his mind to, Jack Donaghy accomplished.

It was ironic, however, realizing that morning that he'd become her friend, someone she talked to and ranted at and unwittingly entrusted with the details of her love life (such as it was). It was most ironic because the previous night, he'd seen Liz Lemon in a restaurant with another man -- an actual boyfriend, who he shook the actual hand of. And who he thoroughly disapproved of, naturally.

And Jack reached a different, rather stunning and very uncomfortable realization.

What had caught him off-guard was the buried stab of jealousy, the faint feeling of indignation. He honestly had not considered that Liz might take a real date to the restaurant he recommended -- or that he, as her boss and new mentor, would even care whom she chose to dine with.

He'd imagined her sitting in the highly exclusive, elitely populated bistro with Jenna or Pete or one of the staff of writers she was so inexplicably fond of. He'd imagined her sitting there in her jeans and glasses, searching the menu for the word 'burger' and not knowing how to pronounce the wine list. He'd imagined her attempting to joke with the maitre'd and dropping food in her lap. He'd imagined her being unable to relax, her eyes darting about and her hands fidgeting, before she left early to catch the end of a '_Laverne and Shirley'_ marathon.

That was the picture in his head, it was very clear. Which incidentally, was a significant part of the problem. Under no circumstances, at any time, for any reason, should Jack Donaghy be picturing Liz Lemon doing anything, however mundane.

What he had not pictured, however, was Liz Lemon sitting in the low candlelight, wearing a simple black dress, her hair all sweet and soft and those intense eyes pleading for him to quit tormenting her and leave already.

While her choice of date was an obvious disaster, which he'd hastened to indicate, Liz herself did not look as out of place as he'd assumed she would. She'd looked nice -- pretty even and until he'd interrupted, she'd looked like she was having a good time. She'd even ordered the swordfish, which he knew was excellent because it was his personal favourite.

It occurred to him, as he walked away with the purple-clad clotheshorse, that, instead of giving her the number and letting her chose her own dinner companion, he could've just taken Lemon to _Stone _himself. It would probably have taken some convincing on his part, but he liked a challenge and it certainly would've beaten the alternative.

Because Jack Donaghy growing instantly, incomprehensibly envious of a man like Dennis, the Beeper King and rat raconteur was not an acceptable state of affairs.

And he _was_ envious. He didn't know from where or when the incitement had come, but on that particular evening, for whatever reason, he felt a definite pang, and regretted giving Lemon that sought-after number. Truthfully, he wanted to be the one leaning across the table towards her, seeing her relaxed and laughing, pulling out her chair, pouring her wine, holding the door for her, escorting her home….

And that's where Jack stopped himself.

Because for the very first time he realized that it might not be so farfetched to suspect that what he really wanted from Liz Lemon was more than simple friendship. And that realization startled him, troubled him, bewildered him.

So when Lemon avoided his gaze the next morning, he followed suit, silently hugging the elevator wall. When she thanked him tightly for the hook-up, he swallowed a smug smile and did not reply. When she yelled at him with all the repressed hostility of the over-scheduled, under-sexed thirty-something he knew her to be, he endured her rage with good grace and bit his tongue.

He refrained from telling her that she deserved more than just a part-time love life. He refrained from telling her that with Dennis, The Beeper King she'd seriously underestimated her own appeal. He refrained from inviting her to accompany _him_ to _Stone_ next time. And, as she continued to rant, he _resolutely _refrained from picturing her in a football sweater -- and only a football sweater. Because picturing was not acceptable, particularly if it had anything to do with Lemon's legs, which were far finer than Jack liked to admit.

Later, when Liz huffed that Dennis looked after her, he also refrained from informing her that she no longer needed Dennis Duffy (or anyone) to look after her because, as far as Jack was concerned, that was his job now. When she stormed into his office, fuming about her idiot boyfriend, he even refrained from using the words 'I told you so'. Instead, he'd pumped her full of conviction he knew she didn't possess and sent her on her wayward way.

And, when Lemon clomped onto the elevator, avoiding his gaze for the second morning in a row, he knew exactly what it meant -- and the pang of jealousy resurfaced. Jack had very little experience with jealousy. He considered the sensation immature and indulgent, not to mention a complete waste of time. And in any instance, it was extremely rare that Jack Donaghy didn't get exactly what he wanted, when he wanted it, how he wanted it.

Apparently, there was a first time for everything.

_TBC…_


	3. Chapter 3

Title: Always a first Time

Author: Mindy

-x-

_Refrain_

The first time he seriously considered kissing Liz Lemon came as a surprise to both of them. It was perhaps not the first time the idea had flitted across his brain, but it was certainly the first time Jack had ever truly considered acting on such an inscrutable impulse.

It was a day full of firsts. When he asked Lemon to attend Gerhardt's birthday party with him, she'd really made him work for it. He'd anticipated that though -- nothing with Lemon was ever simple or easy and he'd pre-prepared a rebuttal for every single excuse she might proffer. He'd instructed Jonathon to verify her schedule so he knew she was free. He made sure to invite her on such short notice that she wouldn't have the chance to freak and back out. He'd organised the dress, jewellery and car. All he needed was Lemon's consent.

To say he was apprehensive about asking her would imply that there was any doubt about the outcome. And to say that he invited her purely for her own betterment would only be half the truth. He truly had wanted to spend an evening with Lemon – he'd wanted that for longer than he cared to acknowledge, even to himself. So, he really wasn't all that bothered that he hadn't had to work so hard for a date since he was a teenager.

The first time Jack saw her in the red dress, he was more than impressed, and didn't bother to hide his surprise. It wasn't so much what the dress did for Lemon as what Lemon did for the dress. He knew when he selected the garment with her in mind that the shade would suit her colouring and the cut would both disguise her imperfections and emphasize the natural endowments she generally hid too well. But he truly hadn't suspected that Lemon had been hiding all those curves beneath layers of navy and denim and spilled food, not to mention a perpetual aura of ragged frustration.

Obviously, he was better than even he knew – and had been paying very close attention to his new protégé. If he were a better boss and less of a man, he would not have spent such time or thought noticing and cataloguing those endowments. Or imagining how she might best accentuate them. But, even in the presence of true inelegance and estranged femininity, Jack was still a man. And part of his duty as a mentor was to develop the particular gifts of each charge.

As it turned out, he could probably have done without the extra accentuation of Lemon's particular gifts. It proved to be a minor distraction that night and more than a little confusing.

He'd tried to delude himself into believing that it was simply the style of the dress that made him want to trace her exposed spine with his fingertips. That it was purely the snug crimson which taunted him into wanting to cup that pear-shaped bottom with both hands and give it a good squeeze. And it was really just the expensive jewels surrounding her pale neck that gave the illusion of Lemon's face lighting up and her eyes twinkling.

It was towards the end of their evening together that it occurred to him that perhaps he'd created an alternate universe Liz Lemon. A woman more accessible, a woman more acceptable -- and it was she who had him falling. It was the Liz of the red dress, the Liz with the diamonds, the Liz who looked almost normal guzzling thousand-dollar champagne by the glassful -- it was she who had him so dazzled and intrigued and slightly disconcerted.

It was party-Liz who was turning his whole evening upside down. The mascara and the heels and the hair had thrown him temporarily, but it was simply an anomalous, transitory attraction. He'd fallen for it before, that mysterious, midnight haze that women could weave around a man's mind with mere feminine tricks of the trade.

Applying such logic to Liz Lemon, though, seemed nothing short of preposterous. There was absolutely nothing about Lemon that was intentionally seductive. If anything, she did all she could that night to keep him at arms length, if not farther. While he was purposefully and covertly seeking to lessen the gap that had always separated their worlds, Lemon was fighting to keep them firmly where they were – safely in the realm of professional friendship.

With all the Bianca business, she was supportive and patient and as a companion she was, as always, entertaining and surprising. But she also made it perfectly clear to him in her own inept way that she was highly uncomfortable with even the idea of anything developing between them.

Lemon's undisguised disinterest, though, only seemed to increase her inexplicable appeal. Jack genuinely hadn't planned to make any move on her when he'd asked her out. But he had to admit to being slightly disappointed by her overly obvious reluctance. Perhaps even a trifle affronted by her barely hidden repulsion.

He usually didn't have that effect on women. He usually didn't hesitate to make a move. And usually, he never doubted the response he would receive in return.

But then, he was usually not interested in women like Liz Lemon. He usually didn't have the chance to get to know her type. He was usually not alone with them, escorting them home after what he considered to be a very successful, very enjoyable evening. Not that there was much about Liz that he would ever class as usual or typical.

Still, when they'd reached that titillating moment of the evening where such moves were made, he felt vaguely illequipped. They'd never been alone like that before and he'd certainly never looked at Lemon the way he found himself doing. He'd never imagined seeing her as more than an acquaintance, more than an employee, more than a slightly frumpy, weirdly amusing writer-type with a special talent for dysfunction.

But there was always a first time.

The relaxed rapport they'd fallen back upon dried up within a millisecond and he saw the uncertainty surface in Lemon's eyes once more. She didn't break the moment or move away. And for a second, Jack simply allowed himself to see her, to really see her -- and to like what he saw.

It occurred to him in that moment, rather unexpectedly, that Liz Lemon was a woman he could truly fall for. That maybe he was halfway there already, without even realising it. And, even more disturbingly, maybe she could detect the truth of it in the flicker of his eyes.

So he stopped, he hesitated. He didn't kiss Lemon.

Even though he'd wanted nothing more. Except perhaps to peel off that devilish red dress, whisk her up in his arms and into the bedroom he knew was just next door. But at the very last moment, Jack refrained. Talk about inscrutable impulses. He'd settled instead for leaning in close and stripping her of her second-hand jewels, his fingertips brushing her skin for the barest moment.

Divesting Lemon of the necklace did not diminish her appeal in the least. It was not all the trappings that he'd forced on her that had produced this effect on him. It was not the borrowed jewellery, the knock-off designer dress or the hasty hair-do that had somehow made Liz Lemon his type. He really was not that susceptible or stupid. Those things had only allowed him to see her differently for one night. The trimmings just acted as a device to draw her closer to him and he wasn't sure he'd ever look at Liz Lemon in quite the same way again.

He would simply have to confess it -- to himself, at the very least. He liked her. Really liked her -- a woman in her late thirties, an egghead, a geek. A wreck of womanhood with poor eyesight, an eating disorder and a big, brazen mouth. He more than liked her -- he wanted her, he adored her. He was utterly entranced by every word, act or deed that tumbled so erratically out of Liz Lemon.

Yet, he'd still hesitated to make a move. It was only as he was walking away from her apartment door, smiling with the perfection of his last quip, that it hit him what he'd done – or rather, what he had not done. Never before had he left a woman's place without getting precisely what he wanted.

And Jack wanted Liz Lemon.

Lord, did he ever. He'd wanted her more than he could ever remember wanting another woman since his tyrant of an ex-wife. But, for some strange reason, he'd stopped himself, second-guessed himself. Jack Donaghy, confirmed ladies man and risk taker extraordinaire, had backed down, chickened out, bailed and run.

Surely, there was a first time for everything.

_TBC…_


	4. Chapter 4

Title: Always a first Time

Author: Mindy

-x-

_Supersede_

The first time Jack recognised he had the ability to make Liz Lemon smile was when he transferred her rival to Connecticut for the sake of her fledging love life. It was not the first benevolent deed he'd orchestrated for her greater good, but it was certainly the one that made Liz sit up and take notice.

He wasn't quite sure what compelled him to do these things for her. And he'd been doing them from the very beginning. Initially, admittedly, it was a deliberate part of his scheme to slowly but surely win over the mercurial writer-type who presented such a challenge to him. To insert himself into her life, to make him somehow indispensable to her, to make her wonder how she ever managed without him. That plan was well on its way towards fruition though. In fact, in Jack's mind, it was game over, target attained, Jack Donaghy, victor and champion. Liz Lemon hadn't stood a chance. She was completely unaware of the miniature war he'd waged or that her mounting esteem was his ultimate prize.

But still he persisted with the strange little acts of kindness. Some she didn't even know about. Some that no one knew about except himself. It had to occur to him that there was something else that motivated him into routinely performing miracles for a woman who was ever only supposed to be a friend. That there might be something else he was seeking, aside from her esteem and friendship. That there was some goal he was working towards that even he himself was unaware of.

There was no doubt that Lemon had become a staple of his day, his one constant and one comfort. She'd gone from humorous offsider to unlikely leading lady in a matter of a short few months. In that time he'd often seen her smirk, scoff, laugh and grin. But until that quiet night, alone in his office, he'd never seen her genuinely smile. Particularly at him. And when she did, he was stunned by the effect it had on him.

Jack was not a stranger to a chivalrous gesture or sagacious deed. He knew precisely what to bestow on whom and when for the effect to be most advantageous. That was part of what made him so good at his job. He knew how to spot a hole in the market and plug it. He could see a problem before it arose and address it. And, likewise, he could systematically and relentlessly woo a woman before she even knew she was within his sights.

Not that he'd had any such intentions when he did what he did for Liz Lemon. It was the furthest thing from his mind, in fact. That was the most extraordinary part about it. He did it to clear her way towards another man. He did it because she was the truest friend he'd had in a long, long time. He did it because if anyone deserved to be happy it was Lemon and it was within his power to make her so. Even if that happiness was fleeting.

Usually when Jack did these things, he always did them with the expectation of receiving something in return. In a business sense, he made these decisions knowing they would lead to advancement and approval. In a romantic sense, he did them because they were the most expeditious way to a woman's heart. And, to be absolutely honest, the rest of her.

Lemon, however, was neither a conquest to be flattered nor a problem to be solved. And couldn't be approached as such. When it came to her, for perhaps the first time in his life, Jack's motives were entirely beyond reproach. What he did for her he did, expecting nothing more in return than what he got. Instead of glowering at him as they normally did, her eyes lit up. And as it dawned on her what he'd done for her, Liz nodded slowly, for once at a complete loss for words, bumbled or otherwise.

And then she smiled. A lop-sided smile, an utterly surprised but totally genuine and truly beguiling smile. He'd spent so long and been so intent on winning her over. But apparently, he was the one who was hooked. Without even touching him, without even coming near him, without even trying to, Liz Lemon made his heart skip a beat.

And that was when he knew. He'd do anything to make her happy. Anything, for that smile.

Jack Donaghy was a model of self-sufficiency. He had always taken care of himself, first and foremost. That's the way he'd functioned for years, even whilst married, and that was the way he liked it. There was only one person in his life who was Numero Uno, and that was himself. Nobody had ever superseded that status. Until now.

Amazingly, there was a first time for everything.

_TBC…_


	5. Chapter 5

Title: Always a First Time

Author: Mindy

_-x-_

_Human_

The first time Colleen met Liz, she liked her instantly and Jack wasn't in the least surprised. His mother might be a lot of things that irked and infuriated him, but he'd never said she was daft. She'd always been a swift and shrewd judge of character. And Jack always suspected that if the two of them met, they would immediately hit it off.

Why he'd considered the possibility was unclear. He purposely permitted his mother as little knowledge of and proximity to his daily life as possible. Most particularly, anyone he genuinely liked was strictly off-limits to her. So while it was natural for her to confuse his protege with his fiancee, it also felt somewhat ironic. Also a little disconcerting. Because before proposing to Phoebe, he'd briefly, privately, very tentatively considered asking for the hand of his unlikely buddy with the remarkable eyes and tenacious strength of character.

For once in his life, his mother would've approved.

Obviously, he'd just been in shock though. His microwaves had been taken away from him in the wake of the fireworks disaster and the man he admired most in the world had all but ordered him remarry. To quickly secure himself a new wife -- a companion, an asset, someone to be there for him through all the trails and tribulations of his advancing career. Strangely enough, when he considered the possibility, the first and only person to come to mind was good old Liz Lemon.

If anyone had told Jack just a few months prior that the bespectacled head writer who couldn't stop glaring at him and wouldn't know make-up if someone actually slapped it on her, would become the most reliable figure in his life -- not to mention a likely prospect for his spouse -- he would've laughed them right out of the building. Then he probably would've called Lemon so she could have a share in the joke. He was, however, greatly surprised to find that the idea of securing her permanent presence at his side did not make him laugh – nor did it make him baulk or cringe or shudder.

He'd never really considered Liz Lemon as marriage material -- not his kind of marriage material anyway. Lemon did not possess the attributes he normally sought in a female companion. But then, he'd had very little success pursuing the glittering, cultured elite. Those relationships, if he could call them that, nearly always ended in humiliation and hostility. Which left him, ultimately, as alone as Lemon was.

Given a choice, he would much rather spend his life with someone than without. And Lemon possessed many traits that more than made up for any minor perceived failings. Plus, he was comfortable with Lemon. He could talk to Lemon. He trusted Lemon. Lemon made him laugh. She brought out the best in him. Don Geiss would love Lemon. His mother would love Lemon. Everyone loved Lemon. Lemon was easy to love. He'd never met someone who grew so quickly and easily on a person. She was so rapidly endearing that it was bizarre.

He might even grow to love Lemon -- really, really love her. Like a normal man might love a normal woman (neither of which he considered them to be). But only if he could convince her to let him try. And therein lay his biggest obstacle. The woman herself.

Jack could sell almost anything to almost anyone. From an early age, he had possessed a strong talent for promotion and persuasion. He was confident he could peddle the idea of matrimony to any woman in the city. Probably any woman in the state. Maybe the country. Possibly the wide world. But, when it came to Liz Lemon, he was at a loss. And that was a definite first.

He tried to reason with himself, convince himself that an offer of marriage to Liz was impractical. That it held little merit and had no basis in reality. For one thing, he doubted Liz would be able fulfil his manifold needs or provide the happiness he deserved. For another, he was even doubtful that he would be capable of making her happy. Frankly, he couldn't conceive of a man who could. He wasn't entirely sure that it was within Lemon's makeup to be happy, to allow a man to make her feel valued and content. And his current effect on her seemed to be mostly the opposite – to make her more frustrated, flustered and insecure than she already was. Which certainly didn't bode well for any future entanglement, however hypothetical.

Jack couldn't ignore the fact that he was never happier or more at ease than in the few minutes a day he shared with Lemon. But he questioned whether that ease and compatibility and trust that they'd cultivated could translate itself into marital bliss. All he knew was, he was not ready to face the prospect of loosing her friendship. However new it might be, it had become an absolute necessity to him. And he was fairly certain that a proposal would put a distinct strain on their now comfortable rapport.

Still, as Jack wandered Christies' pristine corridors and vast galleries, something in him did not wish to release the notion. Being bound legally and emotionally to Liz Lemon (and having her bound to him) apparently held some mysterious appeal for him. In fact, he was still mulling over his peculiar inspiration when Lemon herself showed up, appearing in an actual dress with actual heels and actual earings. If he was not mistaken, she was even wearing make-up.

He could honestly say, for the first time since they'd met, that she looked utterly, effortlessly gorgeous -- in her own way, in a way that he could never have contrived. He didn't actually say it to her, of course. Jack was fundamentally adverse to praise. Needing approval indicated weakness of character. And, in any case, he was fully and irritatingly aware that Lemon's blossoming appearance had nothing whatever to do with his advice and guidance and everything to do with the glow and gloss her new relationship.

Another man was responsible for the foolish grin she was exhibiting and the girlish gleam in her eye, as well as the fact that she had uncharacteristically abandoned him in his time of great need. He could almost find it in his heart to forgive her – if not for the familiar pang he begrudgingly felt at the idea of her with another man. Any other man.

He did his best to hide personal jealousy behind professional betrayal. But he'd never been a good actor and he was unpracticed at dealing with the weight of such emotion. He wasn't sure that a little of the bitterness he was feeling didn't seep through. Liz could tell something was very wrong, she sensed it in his manner almost immediately. And that was peculiar for him -- being known like that, being read so easily. No one had been able to do that with him since Bianca. And even then, she usually only used her insight to gather fresh ammunition on him for their next epic battle.

He had greater faith in Lemon though. He knew she would not do that to him. He knew her concern was genuine, her inherent sincerity waiting patiently for him to reveal what he'd summoned her for. He knew he could trust her with anything. But something in him still resented feeling so transparent, feeling cornered, feeling vulnerable. Even to someone as innocuous as Liz Lemon.

Perhaps he'd spent too many years fearing and fighting injuries inflicted by the Biancas of the world, the fiery femme fatales with nothing on their twisted minds but revenge and domination, that he'd failed to recognise the stealthy threat of a woman like Liz Lemon, who could easily get under a man's skin and consume him from the inside.

Yet when she turned those eyes on him – those dark, inescapable eyes (which incidentally were equally intense with or without the make-up), against his will, he found himself wavering, softening. As much as he may've wished to, Jack couldn't remain angry with her. In that moment, he'd wanted to tell her everything. He'd wanted to spill his guts in a decidedly undignified fashion.

He didn't, of course. Once again, when it came to Liz Lemon, Jack refrained. He held to his time-honored pattern. He held back. He did not tell her of his demotion. He didn't offer to forgive her for her desertion. And he definitely did not share his odd, unshakeable urge to suggest that both their problems might be solved if the two of them got hitched. Primarily his, since she was currently experiencing none.

Perhaps, it was the fear that if he let one problem out, all the others would follow. Perhaps, he feared her holding more sway over him than she already did. Which apparently was more than was healthy for him. He already felt exposed under her scrutiny, feeling things he'd never allowed himself to experience before. Lemon was no expert at reading men but she was certainly no fool, and he didn't want her to guess what lay behind his deliberately disdainful manner.

He didn't want to be feeling what he was feeling. He didn't want to be blaming her, resenting her for following his advice, for pursuing a life she deserved, for looking happy and fulfilled and gorgeous. But that's what he was doing. It was irrational and absurd and excruciatingly plebeian.

He felt pathetic. Weak. Predictable. Human. And he didn't like it one bit. Jack Donaghy didn't do 'human'. Not until Liz Lemon came along. Something had changed, something had shifted and, suddenly, he was feeling as unnervingly human as the next man.

Unfortunately, there was a first time for everything.

TBC...


	6. Chapter 6

Title: Always a First Time

Author: Mindy

A/N: Thanks to those who've read and responded. It's been very encouraging and very useful getting this out there. The juices began to flow better on the second part of this, which I will be posting very shortly. There is one more short chapter in this series to come, so stay tuned.

-x-

_Competition_

The first time Liz Lemon made Jack want to sit on a knife was when she walked into one of his favorite restaurants at the side of a man she'd been mooning over for weeks. Never before had he seen Lemon moon and frankly, in his opinion, it was not her best look. There was something about it that made him feel vaguely….unsettled.

Typically, Lemon paid little to no attention to her personal 'look'. Jack assumed that whatever style she possessed simply occurred by default. In the darkness of her bedroom, in the half-slumber of early morning, her clothes just fell onto her at random. So he imagined. But in the preceding weeks, he'd watched a different 'look' take the place of her usual harried non-style. However accidental it might be, however coincidental he hoped it to be, Lemon had started to dress, look and even smell like a real woman.

Gone were the perpetual jeans and coffee-stained shirts. Gone were the work sneakers, as was the lazy ponytail. And occasionally he even saw her roaming the corridors sans specs. Presumably in case she got onto an elevator with the object of her affection. If he could convince himself that her sudden transformation had anything to do with him, Jack would've been proud. He would've congratulated himself. But it didn't, so he wasn't, and he couldn't.

Also unsettling was the fact that, in the past, romance had been something Liz had been reluctantly pressured into. Frequently by him. He'd been very vocal about encouraging her to improve her love life. He'd even aided her in her quest to woo Flower Guy. And it wasn't like he'd never seen her with men prior to this. She'd had boyfriends, or at least, romantic interests before without them inciting much of a reaction in him. Or in her, really. The new, improved Lemon, however, actually seemed to _want _this particular relationship with this particular man. She'd even invited Jack to meet him. Which certainly implied how important one of them had become to her. Jack just wasn't sure which one.

Even as a child, Jack had never reacted well to sharing his toys -- one character flaw that apparently lingered. But he still took Lemon up on her offer. He was more than eager to size up this new conquest of hers. Not just to see whether the other man was any match for _him_, but also, to see if he was a good match for _her_. He was curious to see what Lemon's idea of her perfect man was -- and if this might be one infatuation that could develop into more. Most importantly though, he'd made it his duty to take care of her best interests. He had to make sure the man she'd chosen was truly deserving of someone as unique as Liz Lemon.

He remembered arriving at the restaurant ridiculously early. He wanted to learn the waiters' names and memorize the layout. He wanted to look so at ease that he might've owned the joint. He also needed a little time to prepare himself -- with plenty and plenty of scotch. The real expensive kind. By nine o'clock, he was feeling no pain – he hoped. And by the time Liz appeared through the chic crowd with the man he assumed to be her Floyd, Jack was feeling both invincible and ready to crumble. Something that was becoming an increasingly familiar sensation when he was around Liz Lemon.

Because, the thing was, he'd prepared himself well. He was ready for the classic Liz Lemon, little black dress with a discreet but alluring glimpse of cleavage. He was prepared for the high heels and the gorgeously uncertain smile and the hair that looked like she'd just rolled out of bed (but hadn't necessarily been sleeping). He was also prepared for the perfume she'd taken to wearing which made her smell less like sandwich meats and more like sin.

Jack had been prepared to smile and hold out his hand when introduced to her new man. He'd prepared himself to spend the evening with someone hideous like Dennis or someone more impressive like the tall guy he'd caught her on the street with once (who was handsome enough that a small part of him felt vaguely threatened). He'd been prepared to see Lemon with someone her own age, someone who looked like he belonged with her, someone as smitten as she had been acting. He'd even prepared an opening crack about the man's name, but then, he was only human.

What he hadn't prepared himself for though, what he'd overlooked, what he'd failed to guard against was that horrid little buried pang. As he watched them approach the table together, he felt it again. That same recurring twinge in his chest. Only stronger now and not so buried -- not so easy to ignore. Another one came when Liz laughed at Floyd's lame joke and neatly tucked her chair in under her little black dress, seating herself right across from him. Another came with the sympathetic look she gave him when he told her about losing the microwaves. Only Lemon could know how deeply that defeat stung.

The pangs came regularly throughout the meal, barely numbed by alcohol as he watched Lemon's eyes constantly turn towards Floyd and Floyd prop his arm on the back of her chair. So persistent were they that he found it far easier to concentrate on her boyfriend than to look at Lemon herself. The only time he did was when she kicked him under the table. He assumed it was accidental but he couldn't help meeting her eyes momentarily, aware that his gaze was lethargic and pitiable. He only hoped she blamed it, and his escalating drunkenness, on his professional heartbreak.

There was one last almost unbearable pang that hit him right in the gut when he watched them leave together. Floyd's hand was resting on Liz's lower back and she grabbed his jacket when she nearly fell off her high heels. Smiling, she ducked her head, her forehead touching his chest, his hand sliding round to her hip. Jack didn't need any sort of imagination to guess how their evening was going to finish. Nor did he need any to imagine how his was. He ordered another scotch. And another dessert.

If he was honest, Jack had been fully prepared to loathe Floyd on the grounds that he was sleeping with a woman he had never had the guts to even make a move on. While she was persistently single with little respite and had seemingly little interest in sex, he hadn't had to worry about it much. But truthfully, he didn't like to think of Liz sleeping with anyone -- except perhaps her team, who regularly fell asleep at their desks. He often found her passed out on her couch after a full nights work, half a dozen sweaty Neanderthal-esque bodies barricading her door like gargoyles.

He was fine with that image. He didn't want it replaced with anything else. He didn't need any other images in his head. He didn't need anyone reminding him that Liz Lemon was an attractive, desirable, delightful and available woman. If slightly unbalanced. It was information Jack had deliberately attempted to block out. But it was becoming harder by the day to maintain his blissful denial.

Unfortunately, Jack also found it difficult to loathe or blame Lemon's new boyfriend. Actually, he quite liked the man -- in an abstract kind of a way. He was a little bland for Lemon but perhaps that was what she wanted. Perhaps she was colorful enough for the both of them. Perhaps she needed someone normal to balance out her insanity. From the outside, it looked like a perfect match. He had to admit she appeared happy. And that was what he had wanted for her.

Still, he wasn't quite sure how either of them missed the barely disguised violence in the painting he gifted Floyd the next day. Jack himself wasn't certain whether Floyd or Liz was meant to be the horse being devoured -- but he was pretty sure who the Lion doing the devouring was.

And like a Lion with lockjaw, he absolutely refused to relinquish his hold on Lemon until it was incontrovertibly clear that he couldn't win. Or, at least until she told him to back off. When Liz informed him so very clearly and crossly that Floyd was taken, what Jack heard was that Lizwas taken. She no longer belonged to him, she apparently never had. And he was no longer the most important man in her everyday life. His instinctive reaction to being replaced was to go on the offensive. To immediately locate a substitute companion. Someone to listen to him and be there for him. Someone more attuned to his needs and more accepting of his affection. Someone with brown hair and nice legs. Someone who would rub Lemon the wrong way, just a little. In much the same way as she'd done to Bianca.

After all, he was a master at people management and this was just another negotiation. It was delicate to be sure and needed to be handled obliquely. But everyone was replaceable. No one was indispensable. And he could prove it. He _would_ prove it, right to Liz Lemon's strangely beguiling face.

When he marched into her office a few days later to apologize he knew exactly what he was doing. As usual, Liz had no idea what was going on. She had no idea there was a game being played out – which gave him a convenient edge. And she had no idea that his ego had crowned her as his current competition. Even he had to acknowledge that was strange. Because if, in the extremely unlikely instance he was actually interested in pursuing Liz Lemon in a romantic sense -- which he'd never admitted to and which posed a whole other set of corresponding problems -- any competitive feeling he might've felt really should've been directed squarely at her lover. Not at her.

But Jack had always possessed an abnormal proclivity for conflict in his relationships with women. Dating was a game. Sex was a competition. And marriage was the ultimate battle. Ever since the disastrous dissolution of his first marriage, he'd wondered whether it was his mother's fault that there existed some bizarre Freudian link for him between sex and animosity. The closer he got to the women in his life, the more intense that proclivity seemed to become. And while the discord in their relationship had eased somewhat, there had always been, from the beginning, an undercurrent of animosity in his interaction with Liz. Not that that necessarily indicted the existence of anything of a sexual nature between them. When it came to Liz Lemon, there had never been any question of sex -- or hope of sex or thought of sex.

Actually though, truth be told, that was not strictly true. Jack could not honestly say he saw Lemon as completely asexual, although sometimes she could be bizarrely naïve on the subject. And there had certainly been moments of intimacy, of clarity that surprised him with their potency. From the outset, he'd been almost irresistibly drawn to her.

There was simply something about a woman who got drunk, told him off and threw things at him on the very same day they met that couldn't help but garner his unswerving attention. And perhaps a little admiration. But that might just have been a strange sort of nostalgia he felt for those early days with Bianca. In any case, it seemed he couldn't subsist in his relationships without some level of conflict. Maybe it gave his ego something to do, something to obsess over, something to conquer. Maybe it just made everything that little bit more exhilarating.

But, whatever the twisted logic, it was the first time his massive competitive streak had reared its ugly head within the teeteringly amicable confines of his alliance with Liz Lemon. Beneath his buoyant exterior, Jack scrutinized Liz's reaction as he told her about his new Floydster. He noticed the way she briefly looked down -- and how forced her enthusiasm was. Secretly, vindictively, he wondered whether his face still showed telltale signs of the quick, mediocre tryst he and Pheobe had just shared against her office door. Not that he assumed Lemon was very practiced at spotting the indications of passion in a man, especially one she wasn't involved with.

Yet, even as he scrutinized her, he still couldn't help but sincerely seek her approval of his chosen one. Even as he silently reveled in his own devious genius, he still needed things to be okay between them. He was completely incapable of telling her this. So he let his competitive streak communicate his affection for him. He was determined to show her. Anything she could do, he could do better. If she could find someone, then so could he. If she could be happy in love, he would be ecstatic in love. He would see her smitten -- and raise her a proposal.

Of course, what Lemon didn't know was that he had been engaged ten times to fourteen different women. Three of those proposals had been to his first wife. They'd finally gotten married just to give themselves something different to argue about and then make up about. Breaking an engagement was simply one more skill to do with the female sex at which Jack was most adept. All it required was the right approach and the perfect infusion of tact and flattery.

Not that he intended his relationship with Pheobe to fail. He was not that cold or calculating. He genuinely was seeking something. He wasn't sure what -- but he'd had many an inspiration while lying in the arms of a fine-looking woman. Evidently, this was not one of those times though. Despite an initial connection, he and Pheobe did not gel. Inspiration was not forthcoming. Perhaps, when he'd met her he was simply feeling a bit needy. Perhaps, he'd been seeking a different brand of intimacy. Perhaps, what he required of a companion had changed materially. Whatever it was he was looking for though, it didn't take long for Jack to realize he was searching for it in entirely the wrong place.

Because of all that had transpired, he could not discuss his relationship woes with his best friend. Their parallel love lives had infused his interaction with Lemon with an oddly nervous energy -- a hesitation, a doubt which had never existed before. Whenever they talked, it felt like there were four people in the room instead of just the two of them. Whenever they were alone, it felt like there was some big question that they were both deliberately not saying out loud. Whatever understanding they'd had was missing. Whatever intimacy they'd been on their way to cementing had also gone the way of Lemon's recent frumpiness.

She was tense around him and he couldn't help but be a little smug. Part of him liked her worrying about him, caring about him. And if she was worrying and caring about him, it left her less time and energy to worry and care about Floyd. Which wasn't to say he was pleased to hear of her boyfriend's sudden departure. Not entirely. Honestly, he felt a little guilty. He'd deliberately inserted himself into their relationship right at the beginning of it, when they should've been bonding. It was a precious time in a new relationship and he'd infected their connection with his overbearing presence. He'd _wanted _to prevent them advancing their intimacy – and it seemed he'd succeeded. There was not much hope of them growing closer while living in different states.

If there was any competition ensuing, it looked like Jack was on the brink of declaring victory. It didn't feel like much of a triumph though. Lemon was no longer mooning her way though the day. Floyd was all but out of the picture. And he was engaged to a beautiful, young, intelligent, impressive young woman who ticked all of his social and political boxes and wore bonkers underwear to bed. He should be happy. By rights, he should've been ecstatic.

But something had been building underneath his close to crumbling facade. All those little pangs had accumulated. All the strain was taking its inevitable toll. One minute, he was talking silk swatches in bed with his fiancée. And the next thing he knew, he was waking up to a silhouette of Liz Lemon. Even fuzzy with drugs, he knew which one he preferred. Even stoned out of his mind, there was one name he could remember, and only one person he absolutely _needed _to see. He couldn't totally see her either. But he could hear her. Her voice made his heartbeat return to normal. Her presence made him breathe easy. And for the first time in some time, when Lemon put her hand on his arm and spoke to him in a quiet, concerned voice, Jack knew that, alone in that hospital room, there really was only the two of them.

Jack had experienced conflict and competition with nearly every woman he was close to and a select few who he wasn't. From his mother and sisters, to his ex-wife and various fiancées, to colleagues and rivals. Liz Lemon was not the first to hate him on sight, glare at him unremorsefully, want to throw things at him or actually throw things at him. Neither was she the first to insult his prowess in the sack, order him to back off or point out how empty his life was. Many had come before her and he was sure at least a few would follow. If someone didn't hate his guts, he wasn't living right.

But what set Lemon apart from all those women, past and future, was one indisputable fact. She _was_, as it turned out, utterly irreplaceable -- as his friend. She did something for him that no one else could or ever had. Despite everything they'd said and put each other through, she was good for him. That was all. Liz Lemon helped mend his slowly awakening heart.

He'd never known anyone like her.

Thankfully, there was a first time for everything.

_TBC..._


	7. Chapter 7

Title: Always a First Time

Author: Mindy

A/N: Sorry for the late update to anyone waiting on this. The first two chapters of the next series are up as well. Enjoy!

_-x-_

_Heart_

The first time Jack admitted to anyone he might have feelings for Liz Lemon beyond those of friendship, he did so to the last person on earth he should've. In his right mind, he would never have let such an important piece of information slip, especially into his mother's hands. She could not be trusted, he'd learnt that at age two.

In his defence, however, he was in a weakened state, having just suffered a minor cardiac event. He was going through what others would describe as a midlife crisis and what he called a lifestyle revitalization. Plus, he was on a cocktail of very heavy-duty drugs. Thankfully, no one else had been in the room to witness the damning admission. Not that that comforted him any.

Colleen had couched a question within half-a-dozen other random but calculated inquires, such as whether he dyed his hair, if and when he'd stolen money from her and whether he loved her. Pheobe had witnessed the beginning of the interrogation but swiftly exited after discovering from his imposed honesty that she was not the love of his life.

Honestly, he thinks she had already started to suspect where his true affections lay. To be more specific, he thinks anyone in frequent contact with him, would've been able to guess his growing attachment to Lemon. Excluding Lemon herself, of course, who was confoundedly oblivious when it came to the opposite sex.

Jack pulled the traitorous little suckers off his chest to prevent any further monitoring of his heart's responses but his merciless mother turned to him with a maniacal grin, having saved her most explosive question for last.

"How do you feel about the Lemon creature?"

Also in his defence, Jack hadn't actually _said_ anything. She couldn't quote him if pressed. He'd neither confirmed nor denied feeling anything at all for Elizabeth Lemon. Apparently, he hadn't needed to. She didn't require an oral confession or even the confirmation of the heart monitor to read his response. His expression confessed everything his doting mother already suspected.

"I thought so," Colleen murmured smugly.

For the first time in…ever, Jack and his mother understood each other completely.

_END. (TBC...)_


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